Trammel, Grace L.; Kuniyil, Rositha; Crook, Phillip F.; Liu, Peng; Brown, M. Kevin published the artcile< Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines>, Electric Literature of 639520-70-0, the main research area is indole derivative preparation nickel catalyzed dearomative arylboration diborane; borylated arylindoline asym preparation; potential energy surface dearomative arylboration indole derivative; azamedicarpin natural product multistep enantioselective preparation.
Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biol. active mols. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermol. dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >40:1 rr and >40:1 dr) from readily available starting materials. Addnl., the origin of regioselectivity was explored exptl. and computationally to uncover the remarkable interplay between carbonyl orientation of the N-protecting group on indole, electronics of the C2-C3 π-bond, and sterics. The method enabled the 1st enantioselective synthesis of (-)-azamedicarpin.
Journal of the American Chemical Society published new progress about Borylation. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Electric Literature of 639520-70-0.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary